The Champions League knockout round begins on Tuesday, with AC Milan set to play host to Tottenham Hotspur for the first leg of their last-16 tie.

Milan returned to winning ways with a narrow victory over Torino on Friday, while the visitors need to pick themselves up after being thrashed 4-1 by Leicester City at the weekend.

AC Milan and Tottenham make a return to the UEFA Champions League (UCL) Round of 16 despite winning just three group stage games each. Both sides have had their troubles domestically, especially reigning Serie A title holders and seven time European champions Milan, who despite the highs of qualifying through a UCL group stage for the first time in nine seasons, now have some ongoing concern about a potential lack of presence in Europe in 2023/24 due to their domestic form.

Although Milan ended their seven-game winless run (D2, L5) across all competitions with a 1-0 Serie A victory against Torino last Friday that took them up to fifth place, some journalists went as far as to speculate about the short-term future of manager Stefano Pioli if his side fail to reach the quarter-finals of the UCL, and/or cannot qualify for the next one courtesy of a top-four finish.

In fact, some Italian publications even reported that Spurs boss Antonio Conte was on a two-man shortlist to be approached at the end of the season by Milan’s ownership.

After enduring a torrid seven-game winless run – which included defeats to their great rivals Inter in both the Italian Super Cup and the league – AC Milan knew only a win would do against Torino in Friday’s Serie A offering.

The Rossoneri had only been knocked out of the Coppa Italia by Ivan Juric’s side last month, but they exacted revenge for that extra-time defeat, with Olivier Giroud heading home just after the hour mark to guide Milan to just their second win of 2023.

Tottenham, UCL runners-up in 2018/19, stormed into this stage with seven points from their last three group stage games, scoring and conceding in all three matches, and the 2-1 win in Marseille during that period would have been especially encouraging as far as this first leg is concerned as Spurs had won just three of their 13 prior UCL away trips (D5, L5).

Ironically, their last meeting with Milan in this competition (2010/11) saw them progress through the Round of 16 with a first leg win at San Siro (1-0) prior to a scoreless draw at White Hart Lane.

Players to watch: Milan’s only goalscorer from the weekend, Olivier Giroud, has netted four times against Tottenham and has a wealth of experience against them. At full-time, he will have notched up more games against Spurs (19) than any other club. Similarly, Tottenham’s Dejan Kulusevski has already taken on Milan seven times – but with very limited success (W1, D2, L4)!

Hot streak: Milan’s last five UCL fixtures were decided by a multiple goal margin (W3, L2).

In contrast, they will not be keen to relive memories created from their most recent last-16 appearance, where they were thumped 4-0 on aggregate by RB Leipzig, which included a miserable 3-0 defeat in the away leg, but that took place under Jose Mourinho’s watch rather Conte, who may be relishing a meeting with an old foe.

Conte’s recent record against Tuesday’s opponents makes for positive reading if you are of a Tottenham persuasion, with eight of his last nine matches against Milan yielding a victory, including a 3-0 win in his most recent away game against the Rossoneri in 2021 when he was manager of their city rivals Inter.

AC Milan Champions League form:

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AC Milan form (all competitions):

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Tottenham Hotspur Champions League form:

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Tottenham Hotspur form (all competitions):

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